Imidazole → 1-Iodomethyl-2-methoxymethylbenzene

HRID 660796Notes

Reaction equation

HRID 660796 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH3:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]O>C(Cl)Cl>[I:25][CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][O:28][CH3:27]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 13681092[2-(Methoxymethyl)phenyl]methanol

Product 1

HCID 688405301-Iodomethyl-2-methoxymethylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidazole (338 mg, 4.98 mmol) and triphenylphosphine (1.3 g, 4.98 mmol) in methylene chloride (10 mL) is added iodine (1.26 g, 4.98 mmol) in portions. The mixture is stirred at RT for 45 min then a solution of (2-methoxymethylphenyl)-methanol (630 mg, 4.14 mmol) in methylene chloride (3 mL) is added dropwise and stirring is continued for 3 h. The mixture is concentrated and the insoluble material is filtered. The filtrate is evaporated and the residue is purified by column chromatography using a gradient of 0-50% EtOAc/hexane as eluent to give the title compound.

Workup

  1. stirringstirring
  2. waitis continued for 3 h
  3. concentrationThe mixture is concentrated
  4. filtrationthe insoluble material is filtered
  5. customThe filtrate is evaporated
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-0bcad41537324fbca28f45d2000b6c94
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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